Portnoy's Complaint (1969) is the American novel that turned its author Philip Roth into a major celebrity, sparking a storm of controversy over its explicit and candid treatment of sexuality, including detailed depictions of masturbation using various props including a piece of liver.[2] The novel tells the humorous monologue of "a lust-ridden, mother-addicted young Jewish bachelor," who confesses to his psychoanalyst in "intimate, shameful detail, and coarse, abusive language."[3][4] Many of its characteristics (comedic prose; themes of sexual desire and sexual frustration; a self-conscious literariness) went on to become Roth trademarks.[citation needed]

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Structurally, Portnoy's Complaint is a continuous monologue as narrated by its speaker, Alexander Portnoy, to his psychoanalyst, Dr. Spielvogel; Roth later explained that the artistic choice to frame the story as a psychoanalytic session was motivated by "the permissive conventions of the patient-analyst situation," which would "permit me to bring into my fiction the sort of intimate, shameful detail, and coarse, abusive language that [...] in another fictional environment would have struck me as pornographic, exhibitionistic, and nothing but obscene."[3][4]

Portnoy is "a lust-ridden, mother addicted young Jewish bachelor,"[3] and the narration weaves through time describing scenes from each stage of his life; every recollection in some way touches upon his central dilemma: his inability to enjoy the fruits of his sexual adventures even as his extreme libidinal urges force him to seek release in ever more creative (and, in his mind, degrading and shameful) acts of eroticism;[citation needed] also, much of his dilemma is that "his sense of himself, his past, and his ridiculous destiny is so fixed".[3] Roth is not subtle about defining this as the main theme of his book. On the first page of the novel, one finds this clinical definition of "Portnoy's Complaint", as if taken from a manual on sexual dysfunction:

" Portnoy's Complaint: A disorder in which strongly felt ethical and altruistic impulses are perpetually warring with extreme sexual longings, often of a perverse nature..."

The title also alludes to the common literary form of complaint, such as The Lover's Complaint, which typically presents the speaker's comments on being a spurned lover.

Other topics touched on in the book include the assimilation experiences of American Jews, their relationship to the Jews of Israel, and the pleasures and perils the narrator sees as inherent in being the son of a Jewish family.

Portnoy's Complaint is also emblematic of the times during which it was published. Most obviously, the book's sexual frankness was both a product of and a reflection on the sexual revolution that was in full swing during the late 1960s. And the book's narrative style, a huge departure from the stately, semi-Jamesian prose of Roth's earlier novels, has often been likened to the stand-up performances of 1960s comedian Lenny Bruce.

The novel is notable for its explicit and candid treatment of sexuality, including detailed depictions of masturbation using various props including a piece of liver[2] which Portnoy's mother later serves for dinner.[6]

Ever since its publication, speculation has abounded as to how much of Portnoy's Complaint is fiction and how much is thinly veiled autobiography. Roth himself pokes fun at these parlor games in his 1981 novelZuckerman Unbound, where alter-ego Nathan Zuckerman is continually accosted by clueless strangers who cannot believe he was exercising the creative faculties of a writer when he wrote the sex scenes in Carnovsky (the alter-novel to Portnoy's Complaint).

Still, by cross-referencing data from interviews, the autobiography of ex-wife Claire Bloom, Roth's own pseudo-autobiography The Facts, and his more biographically mimetic Zuckerman novels, the following can be established about Portnoy's Complaint with a high degree of certainty:

The novel began as a dinner-table comedy routine delivered by Roth to New Republic drama critic Robert Brustein and their circle of mutual New York City friends (The Facts)

Like Portnoy, Roth was heavily influenced as an adolescent by the World War II radio dramas of playwright Norman Corwin. Both teenage Portnoy and teenage Nathan Zuckerman (cf. I Married a Communist) produce politically didactic radio plays as their first forays into literature, and so it is highly likely Roth began his career with a similar work of juvenilia[7]

Portnoy's career as a civil rights attorney reflects Roth's own Popular front-inspired civic idealism; when he was visited by lawyers from the Anti-Defamation League to discuss the controversy over a story in Goodbye, Columbus, Roth recollects that: "As a high school senior thinking about studying law, I had sometimes imagined working on their staff, defending the civil and legal rights of Jews" (The Facts).

The central female character of Portnoy's Complaint, Mary Jane Reed (aka "The Monkey") is a caricature of Roth's first wife, Margaret Martinson. Specifically, the women share the same neurotic need to submerge themselves in Portnoy's/Roth's Jewish identity so as to co-opt some of the same family love that was missing from their own lives (Claire Bloom's Leaving a Doll's House: A Memoir).

The publication of the novel caused a major controversy in American public discourse. The two aspects that evoked such outrage were its explicit and candid treatment about sexuality and obscenities, including detailed depiction of masturbation, which was revolutionary in the late 1960s; and the irreverent portrait of Jewish identity.[4] It sparked an uproar in the Jewish community, even among New York intellectuals such as Irving Howe and Diana Trilling.[4]

In 1969 the book was declared a "prohibited import" in Australia, though the Australian publisher, Penguin Books, resisted and had copies printed up in secret and stored in fleets of moving trucks. Several attempts to prosecute Penguin and any bookseller carrying the book failed.[8]

Many libraries in the United States banned the book because of its detailed discussion of masturbation and its explicit language.[4]

The popularity of the novel has caused the title to become a sort of shorthand for any form of sexual malaise or activity. In his autobiography, Dick Cavett wrote that on one occasion when a male guest was unable to appear on his talk show, Cavett jokingly told the studio audience the guest could not attend because he was "suffering from Portnoy's Complaint", a comment which the network censors decided to cut from the broadcast tape. Gore Vidal once quipped to Claire Bloom, Roth's second wife: "You have already had Portnoy's complaint [her previous husband]. Do not involve yourself with Portnoy."

In the September 8th 2010 edition of the Daily Show, as part of an extended segment on the amount of violence in major religious texts, Jon Stewart and John Oliver have a debate wherein Stewart claims the book as the main text of Judaism, in response to Oliver's demand of disavowal regarding the violence depicted in portions of Hebrew sacred texts.

In her metafictional novel Culture Shock (Duckworth 1988), Valerie Grosvenor Myer wrote of a satirically presented married couple among her characters: "Let us consider my Jean and Jack ... I weighted the scales by presenting them in the rôle of parents ... fictional parents are usually set up as Aunt Sallies to be knocked down ... Mrs Bennet, Mrs Nickleby, Mrs Portnoy; Old Capulet, Mr Dorrit, Dr Sloper."

The Mad Men character, Don Draper, is briefly shown reading the novel in the season seven episode of the series entitled, "The Monolith."